Nitromethane-acetone-adipic acid condensation polymer



Patented July 6, 1948 NITROMETHANE-ACETONE-ADIPIC ACID CONDENSATIONPOLYMER Albin Johnson, Delmar, N. Y., assignor, by mesne assignments, toTel: Hughes, Inc., a corporation of New York No Drawing. ApplicationAugust 5, 1946,

7 Serial N0. 688,429

6 Claims. (Cl. 260-63) My invention relates to a new composition ofmatter and particularly to a new linear condensation polymer, the methodof making it and to the fibers and threads formed therefrom.

One of the objects of my invention is to Provide a new composition ofmatter from which attenuated fibers and threads of high strength may beformed. A further object is to provide a new synthetic thread or fiberwhich in the coarser sizes is well adapted for use in forming artificialbristles for brushes and the like and which may be used in the finersizes in the manufacture of almost any fabric or article heretoforeformed from threads or yarns of organic fiber.

The composition is formed by the reaction of nitromethane, acetone andadipic acid.

In forming my composition, I start with the following ingredients in theproportions indicated-- catalysts, such as calcium hydroxide, bariumhydroxide, powdered zinc, etc., are placed in a vacuum, resin stillwhich can be heated up to at least 250 C. and which can be cooled by airor water to about below the temperature at which the reaction takesplace. The still should be equipped with a stirrer or mixer and alsowith a thermometer for indicating the temperature of the mixture. L

.The ingredients are stirred and heat is gradually applied until thetemperature at which .the reaction occurs is reached, which is about140-l50 C. and will'be evidenced by a sudden rise in temperature.Additional heat is then applied to raise the temperature to about 250 C.The vacuum is also applied to remove the water from the mixture andprevent oxidation, and the mixture is maintained .under the vacuum atabout 250 C., or at least below the temperature at which it willdiscolor, until it thickens to the proper consistency, as determined bytest from time to time. When a stringymass can be drawn out of themixture on a glass rod thrust therein the product may be poured from'thestill and cooled under normal atmospheric conditions. so 2. That stepinthe method of making a syn- Ingredient afi Formula Nitromethane 2 came.

' Acetone lto2 OH;O0OH; u

Adipic Acid 1 ooomomnooon These ingredients, together with say 0.1%(calculated on the total weight of the mixture) of titanium dioxide orany of the other well known 3 When cooled, the mass or sheet of materialis ground to a powder and extruded under heat and pressure to form athread or filament which is thereafter stretched or oriented under heatto increase its strength.

The final thread or filament product is tough, strong and pliable andappears quitesimilar to a "nylon" filament. However, it requires anextruding temperature of at least 280 0., whereas "nylon" may beextruded at temperatures of from about 230 to about 275 C., while fororienting,

my thread must be heated to a temperature of about 150 C. which isconsiderably higher-than that required for nylon." It is impossible toextrude a'mlxture of powdered "nylon" and my product.

Tests of "nylon and my plastic thread, each drawn to a diameter of0.019", show comparative ultimate-tensile strengths as follows whenpulled on a bristle pulling machine.

Plastic Nylon W no 85 100 so 115,. 100 no 12)... 30

densation polymerization treatment until filaments can be drawntherefrom:

Ingredient agg Nigromafhsma Amimm 1 t0 2 Adipic Acid l thetic polymerwhich comprises subjecting the following ingredients inabout theproportions set Ingmdmt mole. forth to a condensation polymerizationtreatclues ment:

5 Nitromethane 2 ima 1 I AdipicAold 1 Ingredient g gg 5. That step inthe method of making a syn- Nitromethane 2 thetic polymer whichcomprises subjecting the figg igi f 9 following ingredients in about theproportions set D forth to a condensation poylmerization treat- 3. Asynthetic polymer formed by subjecting a mixture comprising thefollowing ingredients in about the proportions set forth to acondensation polymerization treatment:

Gram Mole- Ingredient cums Nitromethane Acetone 1 to 2 Adipic Acid lment:

. Gram mole- Ingredient cu! Nitromethane; 2 Acetone 1 Adipic Acid i 6. Asynthetic polymer formed by subjecting a mixture comprising thefollowing ingredients in about the proportions set forth to acondensation polymerization treatment:

ALBIN JOHNSON.

